Triethylamine → HCID 178451792, compound

HRID 2283946Notes

Reaction equation

HRID 2283946 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14](=O)[NH:15][CH2:16][C:17]([C:19]2[CH:24]=[CH:23][C:22]([F:25])=[C:21]([C:26]([F:29])([F:28])[F:27])[CH:20]=2)=O)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C([N:33](CC)CC)C.C([O-])(=O)C.[NH4+]>C(O)CCC.C(OCC)(=O)C>[F:25][C:22]1[CH:23]=[CH:24][C:19]([C:17]2[N:33]=[C:14]([CH:11]3[CH2:12][CH2:13][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH2:9][CH2:10]3)[NH:15][CH:16]=2)=[CH:20][C:21]=1[C:26]([F:29])([F:28])[F:27]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 517165Ammonium AcetateHCID 534391291-Boc-4-(2-(4-Fluoro-3-(trifluoromethyl)phenyl)-2-oxoethylcarbamoyl)piperidine

Product 1

HCID 178451792HCID 178451792, compoundYield 54.1%

Reagents, catalysts & solvents 2

HCID 2631-ButanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 4-[2-(4-Fluoro-3-trifluoromethyl-phenyl)-2-oxo-ethylcarbamoyl]-piperidine-1-carboxylic acid tert-butyl ester (2900.00 mg; 6.71 mmol; 1.00 eq.), triethylamine (0.94 ml; 6.71 mmol; 1.00 eq.), and ammonium acetate (3618.76 mg; 46.95 mmol; 7.00 eq.) in 20 ml of n-butanol was placed in microwave (150° C.) for 20 min. after cooling to rt, the reaction mixture was diluted with 150 ml of ethyl acetate and washed with water, 5% NaHCO3aq, then brine and concentrated. The residue was treated with ether and collected whit solid as title compound (1500 mg, 54% yield).

Workup

  1. washwashed with water, 5% NaHCO3aq
  2. concentrationbrine and concentrated
  3. additionThe residue was treated with ether

Sources & evidence

ORD record
ord-a0a19c6d66964fd2971ea5b056df71f3
Source dataset
uspto-grants-2015_09
Patent number
US09145392B2

Reaction notes

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